Key West Cruises & Sailing Tours - Page 2

62 experiences to discover

Day & Sunset Cruises Dinner Cruises Sailing Trips

Explore the best cruises & sailing tours tours and activities in Key West. Our unbiased ratings help you find the perfect experiences for your trip.

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4.56

Key West Tiki Sunset Cruise 90 min

From $69

1 provider live

Sail on a unique 53-foot tiki boat

Beer, wine and sangria for guests >21 years of age

4.56

Key West Sandbar Cruise on a Tiki Bar Boat 4 hr

From $564

1 provider live

Explore turquoise waters of the Florida Keys

Parking

4.56

Marathon Sunset Cruise

From $89

1 provider live

Experience a breathtaking sunset

Soda/Pop

4.55

Key West Sunset Cruise

From $350

1 provider live

Experience a private sunset cruise

Cooler with ice

4.55

Key West Harbor Sailing Charter

From $395

1 provider live

Sail the scenic Key West harbor

Bottled water

4.55

Key West Tiki Bar Party Boat & Sandbar - 2 hr

From $403

1 provider live

Cruise on a Tiki bar boat

Tiki Boat

4.55

Key West Private Tiki Boat Cruise

From $565

1 provider live

Experience the cool waters of the Florida Keys

A US Coast Guard certified captain

4.55

Key West Private Sunset Charter with Music

From $899

1 provider live

Sail into the sunset

Music and drinks for all visitors

4.54

Key West Hobie Wave Cat Rental

From $105

1 provider live

Sail across the serene Wai Kai Lagoon

1-hour Hobie Wave Cat rental

4.53

Key West Sunset Dinner Cruise with Live Music

From $120

1 provider live

Savor a tropical buffet

2 modern restrooms

4.53

Stock Island Sunset Wine and Sail 2 hr

$134-$135

2 providers combined

Sail into the Floribbean sunset

Premium wine and cold beer

4.52

Key West Windjammer Day Sail

From $50

1 provider live

Sail past Key West's iconic landmarks

Homemade sangria, wine, beer, liquor, soft drinks, and filtered water